Amine-type developer for diazotype materials

ABSTRACT

A DEVELOPER LIQUID CONTAINING AS THE ACTIVE INGREDIENTS AT LEAST 20% BY WEIGHT OF MORPHOLINE, PIPERIDINE, LOWER ALKYL MORPHOLINE, LOWER ALKYL PIPERIDINE, OR AN ORGANIC AMINE OF THE FORMULA:   RR&#39;&#39;N-CNH2N-O-X   WHEREIN R, R&#39;&#39; AND X ARE HYDROGEN, LOWER ALKYL OR LOWER HYDROXY ALKYL AND N IS AN INTEGER FROM 2 TO 4. INCLUSIVE, AND CONTAINING A DILUENT WHICH MAY BE A POLYHYDRIC ALCOHOL, A GLYCOL ETHER OR A MONOFUNCTIONAL ALCOHOL AND A THIRD COMPONENT WHICH IS A CARBOXYLIC FATTY ACID HAVING A CARBON CHAIN LENGTH OF FROM 16 TO 18 CARBON ATOMS SUCH AS OLEIC, LINOLEIC, LINOLENIC, STEARIC OR PALMITIC AND IS PRESENT IN AN AMOUNT RANGING FROM 1% TO 20% BY WEIGHT.

United States Patent Oflice 3,809,560 Patented May 7, 1974 3,809,560AMINE-TYPE DEVELOPER FOR DIAZOTYPE MATERIALS Henry J. Neuman, 5730Sheridan Road,

Chicago, Ill. 60660 No Drawing. Original application Mar. 26, 1971, Ser.No.

128,541, now abandoned. Divided and this application June 8, 1973, Ser.No. 368,573

Int. Cl. G03c 5/34 US. Cl. 96-49 6 Claims ABSTRACT OF rm: DISCLOSURE Adeveloper liquid containing as the active ingredients at least 20% byweight of morpholine, piperidine, lower alkyl morpholine, lower alkylpiperidine, or an organic amine of the formula:

wherein R, R and X are hydrogen, lower alkyl or lower hydroxy alkyl andn is an integer from 2 to 4, inclusive, and containing a diluent whichmay be a polyhydric alcohol, a glycol ether or a monofunctional alcoholand a third component which is a carboxylic fatty acid having a carbonchain length of from 16 to 18 carbon atoms such as oleic, linoleic,linolenic, stearic or palrnitic and is present in an amount ranging from1% to 20% by weight.

This is a division of application Ser. No. 128,541 filed Mar. 26, 1971now abandoned.

BACKGROUND OF THE INVENTION This invention relates to liquid developersfor develop ing two-component diazotype materials in which the activeingredient is an organic amine and more particularly developer liquidcompositions which can be used under conditions where small amounts ofthe liquid are spread over the latent image bearing surface of atwo-component diazotype material.

Diazotype reproduction processes in which a two-component diazotypematerial is developed by applying a small amount of a developer liquid,usually not exceeding three grams per square meter of the latent imagebearing surface are described in US. Pat. 3,446,620, issued to KonradParker on May 27, 1969, and assigned to the same assignee as the instantinvention. This known technique which produces a dry copy directly froma liquid developing step is accomplished by supplying controlled amountsof the concentrated developer solution, comprising an aliphatic amine,to a two-component diazotype material. The technique calls for providinga developing re gion through which is passed the exposed diazotype paperwhere the controlled small amount of liquid is applied directly to thelatent diazo image bearing surface to effectively develop the azo-dyeimage and the prints emerge dry, odor-free and ready for use.

The controlled amounts of liquid refer to the application of quantitiesnot in excess of three grams of developer per square meter of the imagebearing surface and preferably in the range of from about 0.5 grams to 2grams per square meter.

The method which is described in 3,446,620, may be carried out by anumber of different types of apparatus specifically designed to applythe controlled amounts. One such apparatus is described in US.application Ser. No. 831,685 now US. Pat. 3,626,833, assigned to thesame assignee as the instant invention. It will be appreciated that inthe construction of such developing apparatus, the usual and knowntechniques of applying a liquid to a surface are not routinelyaccomplished and require special consideration.

SUMMARY OF THE INVENTION In the circumstance that liquid developer isapplied at the rate of 1 or 2 grams per square meter of the twocomponentdiazotype material, it is necessary that at the developing region theliquid is uniformly and evenly applied so that the azo-dye image whichresults is of a uniform dye density. It has been found that great stressis imposed on such apparatus applying the small amounts of developerliquid which must be uniformly spread over the entire image-bearingsurface area.

Apparatus equipped with applicator rollers whose surface has beenspecially prepared to carry a controlled amount of liquid and operate inconjunction with a squeegee or wiping device to further monitor theamount of liquid, tends to generate high frictional forces at thedeveloping stage. The high frictional stresses at the point ofdevelopment impose a stress on the drive mechanism for the apparatus,which in turn causes erratic movement of the drive rollers. There is aperceptible variation in speed. Thus, the paper to be developed isadvanced through the developer in the same erratic fashion causing imagestriations and irregularities in the copy due to irregular liquidapplication.

It is a general object of this invention to provide an improved liquiddeveloper composition for developing two-component diazotype materialswhich permits the application of very small quantities of said liquid tobe spread uniformly and evenly over the surface of the diazotypematerial.

It is another object of this invention to provide an improved liquiddeveloper composition for developing twocomponent diazotype materialswhich tends to alleviate the stresses imposed on such developingequipment under the conditions of applying less than 3 grams of saiddeveloper liquid to the latent image bearing surface of the diazotypematerial.

It is a specific object of this invention to provide an improveddeveloper liquid composition for developing two-component diazotypematerials employing a concentrated solution of an aliphatic amine, and acarboxylic fatty acid increasing the lubricity of the system to greatlyenhance the uniformity and evenness of application.

The objectives recited above are achieved by a new composition fordeveloper liquids which comprise from 20% to by weight of an activealkaline component such as an aliphatic amine, a diluent comprised of apolyhydric alcohol, a glycol ether or a monofunctional alcohol; and acarboxylic fatty acid having from 16 to 18 carbon atoms in an amountranging from 1% to 20% by weight.

DESCRIPTION OF THE PREFERRED EMBODIMENTS The following description setsforth the details of the developer which will achieve the objects setforth in the Summary of the Invention.

The alkaline component of the developer may be a 1 compound having thegeneral formula:

0 represents a heterocyclic ring such as morpholine and piperidine.

The preferred amines, useful in this invention are those which comewithin the formula:

wherein R and R are the same or different alkyl or hydroxyalkyl radicalsor hydrogen, X is hydrogen, al-kyl or hydroxyalkyl, and n is an integerfrof 2 to 4, inclusive.

The alkaline component may be diluted with a compound selected from thegroup consisting of a polyhydric alcohol, a glycolether, amonofunctional alcohol and water or admixtures thereof. The diluent maybe present in amounts ranging from 17% to 60% by weight of theformulation, the preferred range being from 30% to 50%.

The following amines have been eminently successful in the practice ofthe method: monoethanolamine, isopropanolamine, 2(2-aminoethoxy)ethanol, triethanolamine, diethanolamine,2-amino-2-methyl-l-propanol, N- methylethanolamine,dimethylethanolamine, hexylamine, cyclohexylamine. Other amines havedemonstrated the ability to develop the diazo print such as betahydroxyethyl trimethyl ammonium carbonate, N-arninoethylethanolamine,alkyl substituted morpholine and piperidine, but are somewhat lessdesirable because they have a detectable odor or they tend to adverselyalfect the dye shade.

The use of a diluent aids in the spreadability and wettingv out of thedeveloper across the area to which it is applied. The diluent also findsutility as a material which can be used to adjust the viscosity of thedeveloper liquid so that it can easily be pumped and caused to flowthrough various conduits to bring it to the developing region. Inaddition, if the diluent has a greater volatility than the aliphaticamine, it will tend to evaporated from the surface having a dryingeffect on the thin layer.

The diluent may be comprised of a polyhydric alcohol selected from thefollowing:

hexylene glycol diethylene glycol polyethylene glycol trimethyleneglycol ethylene glycol propylene glycol dipropylene glycol glycerine andglycol-ethers such as:

ethylene glycol monoethyl ether (Cellosolve) diethylene glycol monoethylether diethylene glycol monomethyl ether butyl Cellosolve or amonofunctional alcohol such as:

4-methoxy-4 methyl-pentanol-Z (pentoxyl) 2-ethyl hexanol cyclohexanolisooctyl alcohol hexanol It has been found advantageous to use thepolyhydric alcohols which are completely compatible with the aliphaticamines and do not adversely affect the print quality. Also, polyhydricalcohols such as, for example, hexylene glycol and glycol ethers enhancethe spreadability of the developer liquid.

The advancement of this invention is represented by the addition of athird component such as a carboxylic fatty acid having a carbon chainlength of from 16 to 18 carbon atoms such as, for example, one of thefollowing:

stearic palmitic cis-9-octadecenoic acid cis,cis-9,'12-octadecadienoicacid cis,cis,cis-9,12,15-ctadecatrienoic acid in the range of from 1% to20% by weight, the preferred range being between 3% and 15% by weight.It will be appreciated that the amount of carboxylic fatty acid to beadded to the developer formulation to minimize or substantially decreasethe frictional forces in the developer system may depend in part on theconcentration of organic amine that is employed. It has been found thatat the higher concentrations it may be necessary to warm the developerabove room temperature to keep the carboxylic acid component insolution.

The following examples of developer solutions which may be employed inaccordance with this invention are given for the purpose of illustratingpreferred embodiments of the invention. It will be understood, however,that this invention is not limited to these illustrations andembodiments of developer solutions useful in practicing this invention.

It will be appreciated that the combination of an alkanolamine and acarboxylic fatty acid will produce the salt of the alkanolamine. Forexample, stearic acid will produce the stearate salt ofmonoethanolamine. All percentages are shown as percent by weight unlessotherwise specified.

Example I Percent Monoethanolamine 60 Hexylene glycol v 20Cis-9-octadecenoic acid 20 The ingredients were mixed together in amixing vessel until a uniform solution resulted. The solution wascharged into the developer trough of a developer unit such as disclosedin copending application Ser. No. 831,685 now US. Pat. 3,626,833, whichis assigned to the same assignee as the instant invention.

Example II Percent Monoethanolamine 60 Diethylene glycol monomethylether20 Diethylene glycol monoethylether l7 Stearic acid 7 3 Example IIIPercent 2-(2-aminoethoxy)ethanol 40 Hexylene glycol 25 Diethylene glycolDiethylene glycol monomethylether l0 Cis,cis-9,12-octadecadienoic acid15 Example IV Percent. Diglycol amine 50 Hexylene glycol 25 Diethyleneglycol monomethylether 5 Cis,cis,cis-9,12,15-octadecatrienoic acid 20Example V Percent Diethanolamine 40 Diethylene glycol 30 4-methoxy-4methyl-pentanol-Z 20 Palmitic acid 10 Example VI Percent Morpholine 5Monoethanolamine 10 Dimethylethanolamine 5 Pentoxol solvent 20Cellosolve 20 Hexylene glycol 25 Cis 9-octadecenoic acid 15 Example VIIPercent Monoethanolamine 50 N-methylethanolamine Triethanolamine 10Diethylene glycol monomethylether 10 Cis-9-0ctadecenoic acid 20 ExampleVIII Percent Monoethanolamine 40 Ethylene glycol 30 Glycerine 10 Water10 Cis-9-octadecenoic acid '10 Example 1X Percent Monoethanolamine 40Tetraethylene glycol 30 Diethylene glycol monomethylether 29Cis,cis-9,l2-octadecadienoic acid 1 Example X Percent Diethylenetriamine50 Diethylene glycol monomethylethe 25 Hexylene glycol 24 Stearic acid 1Example XI Percent Hexylamine 50 Hexylene glycol 25 Diethylene glycolCis-9-octadecenoic acid 10 Example XElI Percent Cyclohexylamine 50Diethylene glycol 25 Diethylene glycol monomethylether 10Cis,cis-9,IZ-octadecadienoic acid 15 Example XIII PercentTriethanolamine 30 Monoethanolamine 5 Hexylene glycol 5 Diethyleneglycol monomethylether 50 Cis-9-octadecenoic acid 10 In each of theabove developer solutions, the inclusion of the carboxylic fatty acidcontributed the necessary lubricity so that the developer apparatusemployed resulted in the application of uniform liquid over the area tobe developed in the range of from 0.5 to 3 grams per square meterwithout placing any undue stress on the drive mechanism. The movement ofthe copy sheet through the developer station was uniform and steadywithout experiencing any halting or erratic movement as is experiencedwhen using developer liquids without the carboxylic fatty acid producingstriations and non-uniform azo-dye formation on the surface of thesheet.

What is claimed is:

1. A method for making a reproduction of an original on a two-componentdiazotype copying material comprising the steps of (a) exposing thecopying material to an actinic radiation pattern corresponding to thelight and dark areas on said original, producing a latent image thereon,

(b) feeding a controlled amount of an alkaline liquid medium comprisingat least 20% by weight based on the total alkaline liquid medium of anorganic amine selected from morpholine, piperidine, loweralkylmorpholine, lower alkylpiperidine, and amines of the formula:

wherein R is alkyl, cycloalkyl, alkyl-aryl, alkylol, alkoxy orhydroxyalkoxyalkyl and R and R are alkyl, cycloalk'yl, alkyl-aryl,alkylol, alkoxy, hydroxyalkoxyalkyl or hydrogen, and from 17% to 60% byweight of a diluent in which said organic amine is dissolved, saiddiluent being a polyhydric alcohol, a glycol ether or a monohydricalcohol containing at least 6 carbon atoms, and from 3 to 20% by weightof a carboxylic fatty acid having a carbon chain length of from 16 to 18carbon atoms,

(0) passing said copy material through said region and applying underpressure an amount of said liquid not exceeding 3.0 grams per squaremeter to said latent image bearing surface, said amount of liquid beingevenly and uniformly spread over said area at a temperature such thatthe liquid is not substantially vaporized, and forming an azo-dye imageinstantaneously on said surface, said copy emerging from said region ina dry condition ready for use.

2. The method as set forth in claim 1 wherein said alkaline liquid is analkanolamine and said carboxylic fatty acid is cis-9-octadecenoic acid.

3. The method as set forth in claim 1 wherein said organic amine ispresent in the range of from 20% to by weight.

4. The method as set forth in claim 1 wherein the carboxylic fatty acidis cis,cis-9,l2-octadecadienoic acid.

5. The method as set forth in claim 1 wherein the carboxylic fatty acidis cis,cis,cis-9,12,15-octadecatrienoic acid.

6. The method as set forth in claim 1 wherein the carboxylic fatty acidis stearic acid.

References Cited UNITED STATES PATENTS 3,130,051 4/ 1964 Herrick et al.96-49 2,7 72,972 12/ 6 Herrick et al. 96-75 3,446,620 5/1969 Parker96-49 2,807,545 9/1957 Frederick 96-75 3,202,510 8/ 1965 Hollmaun 96-492,969,015 1/ 1961 Klimkowski et al 96-49 2,865,873 12/ 1958 Hodgins etal 96-49 3,166,421 1/1965 Gramlich 96-49 3,284,201 11/1966 Meijs et al96-49 X 3,355,295 11/1967 Priest 96--49 X 3,578,452 5/1971 Parker 96-49CHARLES L. BOWERS, 111., Primary Examiner UNITED STATES PATENT OFFICECERTIFICATE OF CORRECTION Patent N0 8G9 560 Dated Max 7 1974 Inventor(s)Henry J Neuman It is certified that error appears in theabove-identified patent and that said Letters Patent are herebycorrected as shown below:

The assignee should read Addressogrpph-Multigraph Corporation,

Mount Prospect, 111.; a corporation of Delaware Signed and sealed this1st day of October 1974.

(SEAL) Attest:

McCOY M. GIBSON JR. a c. MARSHALL DANN Commissioner of Patents AttestingOfficer USCOMM-DC 60376-P69 u.s. GOVERNMENT rlmmuc orncz; 930

FORM PO-1Q5O (10-69)

